2.1.1.150: isoflavone 7-O-methyltransferase
This is an abbreviated version!
For detailed information about isoflavone 7-O-methyltransferase, go to the full flat file.
Word Map on EC 2.1.1.150
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2.1.1.150
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isoflavonoids
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alfalfa
-
phytoalexins
-
daidzein
-
medicago
-
sativa
-
medicarpin
-
formononetin
-
pisum
-
phenylpropanoid
-
regiospecific
-
leguminous
-
chalcone
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4'-o-methylated
-
b-rings
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7-hydroxyl
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caffeic
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4'-o-methyltransferase
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7-o-methylation
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cinnamic
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4\'-hydroxyl
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elicitor-induced
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chickpea
-
pterocarpan
-
elicitor-treated
- 2.1.1.150
-
isoflavonoids
- alfalfa
-
phytoalexins
- daidzein
-
medicago
- sativa
- medicarpin
- formononetin
-
pisum
-
phenylpropanoid
-
regiospecific
-
leguminous
- chalcone
-
4'-o-methylated
-
b-rings
-
7-hydroxyl
-
caffeic
-
4'-o-methyltransferase
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7-o-methylation
-
cinnamic
-
4\'-hydroxyl
-
elicitor-induced
- chickpea
-
pterocarpan
-
elicitor-treated
Reaction
Synonyms
7-IOMT, 8-IOMT, HI4'OMT, IOMT, IOMT II, IOMT8, isoflavone methyltransferase, isoflavone O-methyltransferase, methyltransferase, 4'-hydroxyisoflavone, MtIOMT1, MtIOMT2, MtIOMT3
ECTree
2.1.1.150 isoflavone 7-O-methyltransferaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.1.1.150 - isoflavone 7-O-methyltransferase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 7,2'-dihydroxy-4'-methoxyisoflavone
S-adenosyl-L-homocysteine + 2-hydroxy-7,4'-dimethoxyisoflavone
-
i.e. 2'-hydroxyformononetin. 55% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein, about 7% of the activity with 6,7,4'-trihydroxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 12.9% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
-
i.e. genistein. 50% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 49% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 5,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 5,4'-dihydroxy-7-methoxyisoflavone
i.e. genistein. 61% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
(i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
136% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
-
i.e. glycitein. 178% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
preferred substrate
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
35% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 6,7,4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 6,4'-dihydroxy-7-methoxyisoflavone
44% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
41% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,3',4'-trihydroxyisoflavone
S-adenosyl-L-homocysteine + 3',4'-dihydroxy-7-methoxyisoflavone
43% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, 39% of the activity with 7,4'-dihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, 52% the activity with 6,7,4'-trihydroxyisoflavone (i.e. daidzein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxy-6-methoxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-6,7-dimethoxyisoflavone
i.e. glycitein, preferred substrate
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
i.e. dihydrodaidzein. 15.6% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavanone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavanone
i.e. dihydrodaidzein. 70% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
-
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
i.e. isoformononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein
i.e. isoformononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein, about 20% of the activity with 6,7,4'-trihydroxyisoflavone (i.e. glycitein). Key enzyme in the biosynthesis of the phytoalexin medicarpin in Medicago sativa
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein. 4'-O-Methylation of an isoflavonoid intermediate is a key reaction in the biosynthesis of the phytoalexin medicarpin in legumes. However, isoflavone O-methyltransferase from alfalfa converts the isoflavone daidzein to 7-O-methyldaidzein (isoformononetin) in vitro as well as in vivo in unchallenged leaves of transgenic alfalfa ectopically expressing IOMT. In contrast, elicitation of IOMT-overexpressing plants with CuC2 or infecting these plants with Phoma medicaginis leads to greater accumulation of formononetin (4'-O-methyl daidzein) and medicarpin in the leaves than does elicitation or infection of control plants, and no isoformononetin is detected
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The operationally soluble IOMT localizes to endomembranes after elicitation of the isoflavonoid pathway. IOMT colocalizes with the endoplasmic reticulumassociated isoflavone synthase cytochrome P450 to ensure rapid B-ring methylation of the unstable 2,7,4'-trihydroxyisoflavanone product of isoflavone synthase, thereby preventing its dehydration to daidzein and subsequent A-ring methylation by free IOMT. In this way, metabolic channeling at the entry point into isoflavonoid phytoalexin biosynthesis protects an unstable intermediate from an unproductive metabolic conversion
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein, about 20% of the activity with 6,7,4'-trihydroxyisoflavone (i.e. glycitein)
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The activity of alfalfa IOMT as an elicitor-inducible, operationally soluble enzyme with 7-position specificity for daidzein in vitro
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
-
i.e. daidzein. 4'-O-Methylation of an isoflavonoid intermediate is a key reaction in the biosynthesis of the phytoalexin medicarpin in legumes. However, isoflavone O-methyltransferase from alfalfa converts the isoflavone daidzein to 7-O-methyldaidzein (isoformononetin) in vitro as well as in vivo in unchallenged leaves of transgenic alfalfa ectopically expressing IOMT. In contrast, elicitation of IOMT-overexpressing plants with CuC2 or infecting these plants with Phoma medicaginis leads to greater accumulation of formononetin (4'-O-methyl daidzein) and medicarpin in the leaves than does elicitation or infection of control plants, and no isoformononetin is detected
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The operationally soluble IOMT localizes to endomembranes after elicitation of the isoflavonoid pathway. IOMT colocalizes with the endoplasmic reticulumassociated isoflavone synthase cytochrome P450 to ensure rapid B-ring methylation of the unstable 2,7,4'-trihydroxyisoflavanone product of isoflavone synthase, thereby preventing its dehydration to daidzein and subsequent A-ring methylation by free IOMT. In this way, metabolic channeling at the entry point into isoflavonoid phytoalexin biosynthesis protects an unstable intermediate from an unproductive metabolic conversion
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. The activity of alfalfa IOMT as an elicitor-inducible, operationally soluble enzyme with 7-position specificity for daidzein in vitro
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. 21% of the activity with 7,4'-dihydroxy-6-methoxyisoflavone (i.e. glycitein)
i.e. formononetin
-
?
S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone
S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
i.e. daidzein. Preferred substrate
-
-
?
additional information
?
-
-
IOMT II does not catalyse the methylation of apigenin, kaempferol, flavonoids mono-hydroxylated in the 2,3,4,5, or 7 positions, flavanones such as naringenin or coumestans such as coumestrol
-
-
?
additional information
?
-
no activity with apigenin (a flavone), naringenine (a falvanone)
-
-
?
additional information
?
-
-
no activity with apigenin (a flavone), naringenine (a falvanone)
-
-
?
additional information
?
-
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
additional information
?
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
additional information
?
-
no activity with 6,7-dihydroxy-4'-methoxyisoflavone
-
-
?
